{"doi":"10.1248/cpb.31.75","title":"Chemical modification of lactose. XVII. Syntheses of O-.ALPHA.- and O-.BETA.-L-fucopyranosyl-(1.RAR.4)- or -(1.RAR.6)-O-.BETA.-D-galactopyranosyl-(1.RAR.4)-D-glucopyranoses (4'- or 6'-O-.ALPHA.- and -O-.BETA.-L-fucopyranosyllactoses).","abstract":null,"journal":"Chemical and Pharmaceutical Bulletin","year":1983,"id":602179,"datarank":0.31191623125197543,"base_score":2.0794415416798357,"endowment":2.0794415416798357,"self_citation_contribution":0.31191623125197543,"citation_network_contribution":0.0,"self_endowment_contribution":0.31191623125197543,"citer_contribution":0.0,"corpus_percentile":null,"corpus_rank":null,"citation_count":7,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":null,"is_data_producer":false,"deposit_databanks":null,"is_oa":false,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":null,"fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":1544314,"name":"SETSUZO TEJIMA","orcid":null,"position":1,"is_corresponding":false},{"id":1544313,"name":"TAKU CHIBA","orcid":null,"position":0,"is_corresponding":false}],"reference_count":0,"raw_metadata":{"has_enrichment":true,"resolved":true,"title":"Chemical modification of lactose. XVII. Syntheses of O-.ALPHA.- and O-.BETA.-L-fucopyranosyl-(1.RAR.4)- or -(1.RAR.6)-O-.BETA.-D-galactopyranosyl-(1.RAR.4)-D-glucopyranoses (4'- or 6'-O-.ALPHA.- and -O-.BETA.-L-fucopyranosyllactoses).","abstract":"1, 6-Anhydro-2, 2', 3, 3', 6'- and -2, 2', 3, 3', 4'-penta-O-benzyl-β-lactoses (4 and 7) were synthesized from 1, 6-anhydro-2, 2', 3, 3'-tetra-O-benzyl-4', 6'-O-benzylidene-β-lactose (1). Condensation of 4 with 2, 3, 4-tri-O-acetyl-α-L-fucopyranosyl bromide (acetobromofucose) in the conventional Koenigs-Knorr reaction, followed by deacetylation, gave 4'-O-linked trisaccharide derivatives bearing α- and β-L-fucopyranosyl linkages (10 and 15) in 13.4 and 25.6% yields, respectively. Analogous condensation of 7 with acetobromofucose gave a 6'-O-linked, fully protected trisaccharide bearing a β-L-fucopyranosyl linkage (20) in 64% yield. Halide ion-catalyzed condensation of 7 with 2, 3, 4-tri-O-benzyl-α-L-fucopyranosyl bromide gave a trisaccharide derivative bearing an α-L-fucopyranosyl linkage (26) in 51.8% yield. Removal of the protecting groups of 10, 15, 20, and 26 provided the title trisaccharides (14, 19, 25, and 30). 1H- and 13C-NMR spectral data of 14, 19, 25, 30, and synthetic intermediates are also presented.","is_dataset_classified":null,"base_score":2.0794415416798357,"endowment":2.0794415416798357,"datacite_reuse_total":0,"file_count":0,"downloads":0,"views":0,"has_version_chain":false,"is_dataset":false,"is_oa":false,"pmid":"23304386","pmcid":null,"openalex_id":"https://openalex.org/W2314174341","authors":[],"funders":[],"total_grants":0,"fwci":1.7237,"citation_percentile":0.82660359,"influential_citations":0,"citation_trend":[],"oa_status":"bronze","license":null,"oa_locations":[{"url":"https://www.jstage.jst.go.jp/article/cpb1958/31/1/31_1_75/_pdf","host_type":"journal"},{"url":"https://www.jstage.jst.go.jp/article/cpb1958/31/1/31_1_75/_pdf","host_type":"publisher"},{"url":"http://www.jstage.jst.go.jp/article/cpb1958/31/1/31_1_75/_pdf","host_type":"publisher"},{"url":"https://doi.org/10.1248/cpb.31.75","host_type":"journal"}],"fields_of_study":["Carbohydrate Chemistry and Synthesis","Enzyme Production and Characterization","Microbial Metabolites in Food Biotechnology"],"mesh_terms":[],"keywords":["Trisaccharide","Chemistry","Bromide","Yield (engineering)","Stereochemistry","Disaccharide","Benzyl bromide","Acetylation","Derivative (finance)","Lactose","Medicinal chemistry","Organic chemistry","Catalysis","Biochemistry"],"sdg_mappings":[{"sdg_number":0,"sdg_label":"Clean water and sanitation"}],"linked_datasets":[],"clinical_trials":[],"software_tools":[],"database_accessions":[],"source":"live","citation_network_status":"fetched"},"created_at":"2026-07-29T18:33:25.967638Z","pmid":null,"pmcid":null,"fwci":null,"citation_percentile":null,"influential_citations":0,"oa_status":null,"license":null,"views":0,"total_file_size_bytes":0,"version_count":0,"fair_f":null,"fair_a":null,"fair_i":null,"fair_r":null,"fair_zscore":null,"fair_rationale":null,"fair_model":null,"fair_agent_version":null,"fair_fulltext_source":null,"fair_has_llm":null,"fair_computed_at":null,"clinical_trials":[],"software_tools":[],"db_accessions":[],"linked_datasets":[],"topics":[]}